CH641453A5 - 4-acetyl-2-alkoxy-7,7-dimethyl-3-oxabicyclo(4.1.0)heptane und verfahren zu deren herstellung. - Google Patents

4-acetyl-2-alkoxy-7,7-dimethyl-3-oxabicyclo(4.1.0)heptane und verfahren zu deren herstellung. Download PDF

Info

Publication number: CH641453A5
Authority: CH; Switzerland
Prior art keywords: compound; carene; iii; formula; dimethyl
Prior art date: 1978-07-19

Application number

CH664979A

Other languages

German (de)

English (en)

Inventor

Roger Arthur Sheldon

Original Assignee

Shell Int Research

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-07-19

Filing date

1979-07-17

Publication date

1984-02-29

1979-07-17 Application filed by Shell Int Research filed Critical Shell Int Research

1984-02-29 Publication of CH641453A5 publication Critical patent/CH641453A5/de

Links

238000000034 method Methods 0.000 title claims description 21
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 26
XCIZLAMMPDJKRZ-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-ol Chemical compound C1C(O)C(C)=CC2C(C)(C)C12 XCIZLAMMPDJKRZ-UHFFFAOYSA-N 0.000 claims description 16
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
BQOFWKZOCNGFEC-BDAKNGLRSA-N (+)-Delta3-carene Chemical compound C1C(C)=CC[C@H]2C(C)(C)[C@@H]12 BQOFWKZOCNGFEC-BDAKNGLRSA-N 0.000 claims description 7
229930006713 (+)-car-3-ene Natural products 0.000 claims description 7
BQOFWKZOCNGFEC-UHFFFAOYSA-N Delta3-Carene Natural products C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
-1 Cyclopropane compound Chemical class 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 5
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 5
150000002148 esters Chemical class 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000002728 pyrethroid Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000006385 ozonation reaction Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000008246 gaseous mixture Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
238000005949 ozonolysis reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
LLMLSUSAKZVFOA-NJGYIYPDSA-N (1r,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(O)=O LLMLSUSAKZVFOA-NJGYIYPDSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
AGHSZSJVJPSERC-UHFFFAOYSA-N 3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane Chemical compound C1C2OC2(C)CC2C(C)(C)C21 AGHSZSJVJPSERC-UHFFFAOYSA-N 0.000 description 1
ZMXYGCYMIHDLLW-UHFFFAOYSA-N 3-hydroxy-7,7-dimethylbicyclo[4.1.0]heptan-4-one Chemical compound C1C(O)C(=O)CC2C(C)(C)C21 ZMXYGCYMIHDLLW-UHFFFAOYSA-N 0.000 description 1
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001942 cyclopropanes Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
- C07C49/507—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic
- C07C49/513—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyrane Compounds (AREA)

CH664979A 1978-07-19 1979-07-17 4-acetyl-2-alkoxy-7,7-dimethyl-3-oxabicyclo(4.1.0)heptane und verfahren zu deren herstellung. CH641453A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7830370		1978-07-19

Publications (1)

Publication Number	Publication Date
CH641453A5 true CH641453A5 (de)	1984-02-29

Family

ID=10498523

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH664979A CH641453A5 (de)	1978-07-19	1979-07-17	4-acetyl-2-alkoxy-7,7-dimethyl-3-oxabicyclo(4.1.0)heptane und verfahren zu deren herstellung.

Country Status (10)

Country	Link
US (1)	US4235785A (da)
JP (1)	JPS5515486A (da)
BE (1)	BE877748A (da)
CA (1)	CA1134375A (da)
CH (1)	CH641453A5 (da)
DE (1)	DE2928840A1 (da)
DK (1)	DK300079A (da)
FR (1)	FR2431493A1 (da)
GB (1)	GB2025966B (da)
NL (1)	NL7905557A (da)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1374244A (en) *	1970-12-24	1974-11-20	Nat Res Dev	Cyclopropane derivatives

1979
- 1979-07-09 US US06/055,856 patent/US4235785A/en not_active Expired - Lifetime
- 1979-07-17 BE BE0/196341A patent/BE877748A/fr not_active IP Right Cessation
- 1979-07-17 GB GB7924886A patent/GB2025966B/en not_active Expired
- 1979-07-17 NL NL7905557A patent/NL7905557A/nl not_active Application Discontinuation
- 1979-07-17 CA CA000331951A patent/CA1134375A/en not_active Expired
- 1979-07-17 FR FR7918458A patent/FR2431493A1/fr active Granted
- 1979-07-17 JP JP8994979A patent/JPS5515486A/ja active Pending
- 1979-07-17 DE DE19792928840 patent/DE2928840A1/de not_active Withdrawn
- 1979-07-17 CH CH664979A patent/CH641453A5/de not_active IP Right Cessation
- 1979-07-17 DK DK300079A patent/DK300079A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
US4235785A (en)	1980-11-25
DK300079A (da)	1980-01-20
JPS5515486A (en)	1980-02-02
DE2928840A1 (de)	1980-01-31
NL7905557A (nl)	1980-01-22
GB2025966A (en)	1980-01-30
FR2431493B1 (da)	1982-11-19
CA1134375A (en)	1982-10-26
GB2025966B (en)	1982-10-13
BE877748A (fr)	1980-01-17
FR2431493A1 (fr)	1980-02-15

Legal Events

Date	Code	Title	Description
1985-03-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

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DE2034128C2 (de)	1986-08-07	Cyclopentenolonester, Cyclopentenone und die Verwendung der Cyclopentenolonester als Insektizide
DE2432235C2 (de)	1984-07-19	Verfahren zur Herstellung von Lavandulol, seinen Estern und von 3,5,5-Trimethyl-hepta-1,6-dien-3-ol
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DE2159882A1 (da)	1972-07-06
DE2013924A1 (de)	1970-10-01	Verfahren zur Razemisierung optisch aktiver trans-Cyclopropancarbonsäuren und ihrer Derivate
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DE2542377C3 (de)	1980-10-02	!,l.l-Trihalogen^-methyl-S-penten-2-ole und Verfahren zu ihrer Herstellung
CH641453A5 (de)	1984-02-29	4-acetyl-2-alkoxy-7,7-dimethyl-3-oxabicyclo(4.1.0)heptane und verfahren zu deren herstellung.
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CH641137A5 (de)	1984-02-15	2-(2,2-dihalogenvinyl-3,3-dimethylcyclopropyl)aethanale und verfahren zur herstellung derselben.
DE2439742C3 (de)	1978-02-16	Verfahren zur Herstellung von Cyclopentenonderivaten
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DE1593380C3 (de)	1975-04-17	Verfahren zur Herstellung von 2-Acetyl-6,6-dimethyl-bicyclo eckige Klammer auf 3,1,0 eckige Klammer zu -2-hexen